I would start out on a Dr Grabow. They are cheap and are PRE SMOKED meaning there is a cake already built up in the bowl and there is no breaking in period. They stick the bowls up to a machine and suck burning tobacco smoke through them until a cake is built up. I still smoke my grabows every once in a while. Premium more expensive pipes are great but you have to break them in. And I would get a pipe you can put pipe filters in while you smoke until you get used to it because it is completely different from cigar smoking. you have a really loose draw, And from time to time alot of relights but with the right tobacco smoking a pipe can be a great experience.